New diterpenoids from Callicarpa dichotoma and their anti-inflammatory activity

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-06-07 DOI:10.1016/j.fitote.2025.106666

Qiaomiao Fang , Xueer Zhang , Minhua Feng, Weiqun Yang, Guangtian Peng, Zhongxiang Zhao, Chaozhan Lin, Chenchen Zhu, Aizhi Wu

{"title":"New diterpenoids from Callicarpa dichotoma and their anti-inflammatory activity","authors":"Qiaomiao Fang , Xueer Zhang , Minhua Feng, Weiqun Yang, Guangtian Peng, Zhongxiang Zhao, Chaozhan Lin, Chenchen Zhu, Aizhi Wu","doi":"10.1016/j.fitote.2025.106666","DOIUrl":null,"url":null,"abstract":"<div><div>Callicarpa dichotoma is a distinctive herbal plant of the genus Callicarpa. However, research on the phytochemical and pharmacological properties of C. dichotoma is very limited. Presently, three new diterpenoids, named dichotomapene A − C(1–3), along with fourteen known analogues (4–17), were isolated from C. dichotoma. Their structures were elucidated by spectroscopy, quantum chemical electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. Compound 1 was an unusual abietane-type diterpenoid with a five-membered lactone ring formed between C-6 and C-18. The undescribed crystal structures of compounds 4, 6, and 13 were obtained for the first time. The anti-inflammatory activity of six diterpenoids on RAW 264.7 murine macrophages induced by LPS was further investigated by measuring the secretion of nitric oxide (NO). Cytotoxic experiments manifested that compound 14 had significant toxicity on RAW 264.7 cells. Griess assay results indicated that compound 7 displayed the best anti-inflammatory activity among five diterpenoids. Furthermore, molecular docking analysis was conducted to interpret the anti-inflammatory mechanism of 7 interacted with inducible nitric oxide synthase(iNOS). This study is the first investigation of diterpenoids within C. dichotoma.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"184 ","pages":"Article 106666"},"PeriodicalIF":2.5000,"publicationDate":"2025-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Fitoterapia","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0367326X25002916","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}

引用次数: 0

Abstract

Callicarpa dichotoma is a distinctive herbal plant of the genus Callicarpa. However, research on the phytochemical and pharmacological properties of C. dichotoma is very limited. Presently, three new diterpenoids, named dichotomapene A − C(1–3), along with fourteen known analogues (4–17), were isolated from C. dichotoma. Their structures were elucidated by spectroscopy, quantum chemical electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. Compound 1 was an unusual abietane-type diterpenoid with a five-membered lactone ring formed between C-6 and C-18. The undescribed crystal structures of compounds 4, 6, and 13 were obtained for the first time. The anti-inflammatory activity of six diterpenoids on RAW 264.7 murine macrophages induced by LPS was further investigated by measuring the secretion of nitric oxide (NO). Cytotoxic experiments manifested that compound 14 had significant toxicity on RAW 264.7 cells. Griess assay results indicated that compound 7 displayed the best anti-inflammatory activity among five diterpenoids. Furthermore, molecular docking analysis was conducted to interpret the anti-inflammatory mechanism of 7 interacted with inducible nitric oxide synthase(iNOS). This study is the first investigation of diterpenoids within C. dichotoma.

查看原文本刊更多论文

新二萜类化合物及其抗炎活性研究

万里莲是万里莲属的一种独特的草本植物。然而，对其植物化学和药理特性的研究非常有限。目前，从二叉木中分离到3个新的二萜类化合物，命名为二叉木apene A−C（1-3）和14个已知的类似物（4-17）。通过光谱学、量子化学电子圆二色性（ECD）计算和单晶x射线衍射分析对其结构进行了表征。化合物1是一种罕见的二萜，在C-6和C-18之间形成一个五元内酯环。化合物4、6和13的晶体结构为首次得到。通过测定一氧化氮（NO）的分泌，进一步研究六种二萜对LPS诱导的小鼠巨噬细胞的抗炎活性。细胞毒实验表明，化合物14对RAW 264.7细胞有明显的毒性作用。Griess实验结果表明，化合物7在5种二萜类化合物中抗炎活性最强。此外，通过分子对接分析来解释7与诱导型一氧化氮合酶（iNOS）相互作用的抗炎机制。本研究首次对二萜进行了研究。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.